Cytotoxic cytochalasins from the endozoic fungus Phoma sp. of the giant jellyfish Nemopilema nomurai
Four new cytochalasin derivatives (1–4), together with cytochalasin B (5), were isolated from the fungus Phoma sp. obtained from the giant jellyfish Nemopilema nomurai. The planar structure and relative stereochemistry were established by analysis of 1D and 2D NMR data. The absolute configuration wa...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2012-05, Vol.22 (9), p.3126-3129 |
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| container_title | Bioorganic & medicinal chemistry letters |
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| creator | Kim, Eun La Li, Jian Lin Dang, Hung The Hong, Jongki Lee, Chong-Ok Kim, Dong-Kyoo Yoon, Won Duk Kim, Euikyung Liu, Yonghong Jung, Jee H. |
| description | Four new cytochalasin derivatives (1–4), together with cytochalasin B (5), were isolated from the fungus Phoma sp. obtained from the giant jellyfish Nemopilema nomurai. The planar structure and relative stereochemistry were established by analysis of 1D and 2D NMR data. The absolute configuration was defined by the modified Mosher’s method. The compounds showed significant cytotoxicity against a small panel of human solid tumor cell lines (A549, SK-OV-3, SK-MEL-2, XF 498, and HCT15) with IC50 values in the range of 0.5–30μM. The cytochalasin B (5) showed obvious cytotoxicity with IC50 of 7.9μM against HeLa human cervical carcinoma cells. |
| doi_str_mv | 10.1016/j.bmcl.2012.03.058 |
| format | Article |
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The planar structure and relative stereochemistry were established by analysis of 1D and 2D NMR data. The absolute configuration was defined by the modified Mosher’s method. The compounds showed significant cytotoxicity against a small panel of human solid tumor cell lines (A549, SK-OV-3, SK-MEL-2, XF 498, and HCT15) with IC50 values in the range of 0.5–30μM. The cytochalasin B (5) showed obvious cytotoxicity with IC50 of 7.9μM against HeLa human cervical carcinoma cells.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2012.03.058</identifier><identifier>PMID: 22483395</identifier><language>eng</language><publisher>Amsterdam: Elsevier Ltd</publisher><subject>Animals ; Antineoplastic agents ; Antineoplastic Agents - chemistry ; Ascomycota - chemistry ; Biological and medical sciences ; Cell Death - drug effects ; Cell Line, Tumor ; Cytochalasin ; cytochalasin B ; Cytochalasins - chemistry ; Cytochalasins - pharmacology ; Cytotoxicity ; Dose-Response Relationship, Drug ; Early Detection of Cancer ; fungi ; General pharmacology ; Humans ; Inhibitory Concentration 50 ; Jellyfish-derived fungus ; Medical sciences ; Miscellaneous ; Molecular Structure ; Nemopilema nomurai ; nuclear magnetic resonance spectroscopy ; Pharmacology. Drug treatments ; Phoma ; Phoma sp ; Scyphozoa ; Scyphozoa - microbiology ; stereochemistry ; uterine cervical neoplasms</subject><ispartof>Bioorganic & medicinal chemistry letters, 2012-05, Vol.22 (9), p.3126-3129</ispartof><rights>2012 Elsevier Ltd</rights><rights>2015 INIST-CNRS</rights><rights>Copyright © 2012 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c476t-a6a45f93eee323ab7ed9a6ce702e075ab92061726f0e721015ac3677c4d5cf493</citedby><cites>FETCH-LOGICAL-c476t-a6a45f93eee323ab7ed9a6ce702e075ab92061726f0e721015ac3677c4d5cf493</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bmcl.2012.03.058$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=25855058$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/22483395$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kim, Eun La</creatorcontrib><creatorcontrib>Li, Jian Lin</creatorcontrib><creatorcontrib>Dang, Hung The</creatorcontrib><creatorcontrib>Hong, Jongki</creatorcontrib><creatorcontrib>Lee, Chong-Ok</creatorcontrib><creatorcontrib>Kim, Dong-Kyoo</creatorcontrib><creatorcontrib>Yoon, Won Duk</creatorcontrib><creatorcontrib>Kim, Euikyung</creatorcontrib><creatorcontrib>Liu, Yonghong</creatorcontrib><creatorcontrib>Jung, Jee H.</creatorcontrib><title>Cytotoxic cytochalasins from the endozoic fungus Phoma sp. of the giant jellyfish Nemopilema nomurai</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>Four new cytochalasin derivatives (1–4), together with cytochalasin B (5), were isolated from the fungus Phoma sp. obtained from the giant jellyfish Nemopilema nomurai. The planar structure and relative stereochemistry were established by analysis of 1D and 2D NMR data. The absolute configuration was defined by the modified Mosher’s method. The compounds showed significant cytotoxicity against a small panel of human solid tumor cell lines (A549, SK-OV-3, SK-MEL-2, XF 498, and HCT15) with IC50 values in the range of 0.5–30μM. The cytochalasin B (5) showed obvious cytotoxicity with IC50 of 7.9μM against HeLa human cervical carcinoma cells.</description><subject>Animals</subject><subject>Antineoplastic agents</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Ascomycota - chemistry</subject><subject>Biological and medical sciences</subject><subject>Cell Death - drug effects</subject><subject>Cell Line, Tumor</subject><subject>Cytochalasin</subject><subject>cytochalasin B</subject><subject>Cytochalasins - chemistry</subject><subject>Cytochalasins - pharmacology</subject><subject>Cytotoxicity</subject><subject>Dose-Response Relationship, Drug</subject><subject>Early Detection of Cancer</subject><subject>fungi</subject><subject>General pharmacology</subject><subject>Humans</subject><subject>Inhibitory Concentration 50</subject><subject>Jellyfish-derived fungus</subject><subject>Medical sciences</subject><subject>Miscellaneous</subject><subject>Molecular Structure</subject><subject>Nemopilema nomurai</subject><subject>nuclear magnetic resonance spectroscopy</subject><subject>Pharmacology. Drug treatments</subject><subject>Phoma</subject><subject>Phoma sp</subject><subject>Scyphozoa</subject><subject>Scyphozoa - microbiology</subject><subject>stereochemistry</subject><subject>uterine cervical neoplasms</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kUuv0zAQRi0E4pYLf4AFZIPEJmHiVxKJDap4SVeABFdiZ02dcesqiYudIMqvx6UFdqw8ks98Mz5m7HENVQ21frGvNqMdKg41r0BUoNo7bFVLLUshQd1lK-g0lG0nv16xByntAWoJUt5nV5zLVohOrVi_Ps5hDj-8LWyu7A4HTH5KhYthLOYdFTT14WfI926ZtksqPu3CiEU6VEVwv4Gtx2ku9jQMR-fTrvhAYzj4gTI1hXGJ6B-yew6HRI8u5zW7ffP6y_pdefPx7fv1q5vSykbPJWqUynWCiAQXuGmo71BbaoATNAo3HQddN1w7oIZnBQqt0E1jZa-sk524Zs_PuYcYvi2UZjP6ZPNiOFFYkqkB2pYLaOqM8jNqY0gpkjOH6EeMxwyZk12zNye75mTXgDDZbm56cslfNiP1f1v-6MzAswuAyeLgIk7Wp3-capU6Bz09cw6DwW3MzO3nPEnlLxKat6envDwTlH199xRNsp4mS72PZGfTB_-_TX8BI3miRg</recordid><startdate>20120501</startdate><enddate>20120501</enddate><creator>Kim, Eun La</creator><creator>Li, Jian Lin</creator><creator>Dang, Hung The</creator><creator>Hong, Jongki</creator><creator>Lee, Chong-Ok</creator><creator>Kim, Dong-Kyoo</creator><creator>Yoon, Won Duk</creator><creator>Kim, Euikyung</creator><creator>Liu, Yonghong</creator><creator>Jung, Jee H.</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>FBQ</scope><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20120501</creationdate><title>Cytotoxic cytochalasins from the endozoic fungus Phoma sp. of the giant jellyfish Nemopilema nomurai</title><author>Kim, Eun La ; Li, Jian Lin ; Dang, Hung The ; Hong, Jongki ; Lee, Chong-Ok ; Kim, Dong-Kyoo ; Yoon, Won Duk ; Kim, Euikyung ; Liu, Yonghong ; Jung, Jee H.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c476t-a6a45f93eee323ab7ed9a6ce702e075ab92061726f0e721015ac3677c4d5cf493</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Animals</topic><topic>Antineoplastic agents</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Ascomycota - chemistry</topic><topic>Biological and medical sciences</topic><topic>Cell Death - drug effects</topic><topic>Cell Line, Tumor</topic><topic>Cytochalasin</topic><topic>cytochalasin B</topic><topic>Cytochalasins - chemistry</topic><topic>Cytochalasins - pharmacology</topic><topic>Cytotoxicity</topic><topic>Dose-Response Relationship, Drug</topic><topic>Early Detection of Cancer</topic><topic>fungi</topic><topic>General pharmacology</topic><topic>Humans</topic><topic>Inhibitory Concentration 50</topic><topic>Jellyfish-derived fungus</topic><topic>Medical sciences</topic><topic>Miscellaneous</topic><topic>Molecular Structure</topic><topic>Nemopilema nomurai</topic><topic>nuclear magnetic resonance spectroscopy</topic><topic>Pharmacology. Drug treatments</topic><topic>Phoma</topic><topic>Phoma sp</topic><topic>Scyphozoa</topic><topic>Scyphozoa - microbiology</topic><topic>stereochemistry</topic><topic>uterine cervical neoplasms</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kim, Eun La</creatorcontrib><creatorcontrib>Li, Jian Lin</creatorcontrib><creatorcontrib>Dang, Hung The</creatorcontrib><creatorcontrib>Hong, Jongki</creatorcontrib><creatorcontrib>Lee, Chong-Ok</creatorcontrib><creatorcontrib>Kim, Dong-Kyoo</creatorcontrib><creatorcontrib>Yoon, Won Duk</creatorcontrib><creatorcontrib>Kim, Euikyung</creatorcontrib><creatorcontrib>Liu, Yonghong</creatorcontrib><creatorcontrib>Jung, Jee H.</creatorcontrib><collection>AGRIS</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kim, Eun La</au><au>Li, Jian Lin</au><au>Dang, Hung The</au><au>Hong, Jongki</au><au>Lee, Chong-Ok</au><au>Kim, Dong-Kyoo</au><au>Yoon, Won Duk</au><au>Kim, Euikyung</au><au>Liu, Yonghong</au><au>Jung, Jee H.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Cytotoxic cytochalasins from the endozoic fungus Phoma sp. of the giant jellyfish Nemopilema nomurai</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2012-05-01</date><risdate>2012</risdate><volume>22</volume><issue>9</issue><spage>3126</spage><epage>3129</epage><pages>3126-3129</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>Four new cytochalasin derivatives (1–4), together with cytochalasin B (5), were isolated from the fungus Phoma sp. obtained from the giant jellyfish Nemopilema nomurai. The planar structure and relative stereochemistry were established by analysis of 1D and 2D NMR data. The absolute configuration was defined by the modified Mosher’s method. The compounds showed significant cytotoxicity against a small panel of human solid tumor cell lines (A549, SK-OV-3, SK-MEL-2, XF 498, and HCT15) with IC50 values in the range of 0.5–30μM. The cytochalasin B (5) showed obvious cytotoxicity with IC50 of 7.9μM against HeLa human cervical carcinoma cells.</abstract><cop>Amsterdam</cop><pub>Elsevier Ltd</pub><pmid>22483395</pmid><doi>10.1016/j.bmcl.2012.03.058</doi><tpages>4</tpages></addata></record> |
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| ispartof | Bioorganic & medicinal chemistry letters, 2012-05, Vol.22 (9), p.3126-3129 |
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| subjects | Animals Antineoplastic agents Antineoplastic Agents - chemistry Ascomycota - chemistry Biological and medical sciences Cell Death - drug effects Cell Line, Tumor Cytochalasin cytochalasin B Cytochalasins - chemistry Cytochalasins - pharmacology Cytotoxicity Dose-Response Relationship, Drug Early Detection of Cancer fungi General pharmacology Humans Inhibitory Concentration 50 Jellyfish-derived fungus Medical sciences Miscellaneous Molecular Structure Nemopilema nomurai nuclear magnetic resonance spectroscopy Pharmacology. Drug treatments Phoma Phoma sp Scyphozoa Scyphozoa - microbiology stereochemistry uterine cervical neoplasms |
| title | Cytotoxic cytochalasins from the endozoic fungus Phoma sp. of the giant jellyfish Nemopilema nomurai |
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